With the widespread uptake of social media, discourses and practices of self-branding have become a pervasive feature of social and economic life. However, the way in which the digital self-brand gets reproduced across a sprawling social media landscape remains comparatively under-theorized. Our paper therefore draws upon in-depth interviews with 52 online content creators—including designers, artists, writers, and marketing consultants—to examine how cultural workers present themselves across the panoply of social networking sites. As we show, workers’ self-presentation activities were structured through the production of a platform-specific self-brand, which was based upon the imaginations of (1) platform affordances, (2) audiences, and (3) the producer’s own self-concept. Our findings highlight producers’ compulsion to engage in continuous, cross-platform labor—despite widespread uncertainty about its economic outcomes. We conclude by addressing the stakes of a social media moment when workers of all stripes are prodded to incessantly curate, monitor, and ultimately invest in their online personae.